(E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide

Base Information

• Chemical Name: (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide
• CAS No.: 1253917-10-0
• Molecular Formula: C₂₅H₃₄N₄O₄S
• Molecular Weight: 486.635

Synonyms:(E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide

Chemical Property of (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide

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Technology Process of (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide

There total 5 articles about (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

2-cyclohexyl-8-(vinylsulfonyl)-1,3,8-triazaspiro[4.5]dec-1-en-4-one (1253926-01-0) + N-(4-bromo-3,5-dimethylphenyl)acetamide (64835-48-9) → (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide (1253917-10-0)

Guidance literature:

With N-Methyldicyclohexylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In 1-methyl-pyrrolidin-2-one; at 110 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00182

Reference yield:

tert-butyl 4-cyano-4-(cyclohexanecarboxamido)piperidine-1-carboxylate → (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide (1253917-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide; dihydrogen peroxide / water; ethanol / 4 h / 80 °C

2: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

3: triethylamine / dichloromethane / 1 h / 0 - 20 °C

4: bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; N-Methyldicyclohexylamine / 1-methyl-pyrrolidin-2-one / 1.5 h / 110 °C / Inert atmosphere

With hydrogenchloride; N-Methyldicyclohexylamine; dihydrogen peroxide; triethylamine; sodium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; 4: |Heck Reaction;

DOI:10.1021/acs.jmedchem.8b00182

Reference yield:

4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (331281-25-5) → (E)-N-(4-(2-((2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)-3,5-dimethylphenyl)acetamide (1253917-10-0)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

2: sodium hydroxide; dihydrogen peroxide / water; ethanol / 4 h / 80 °C

3: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

4: triethylamine / dichloromethane / 1 h / 0 - 20 °C

5: bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; N-Methyldicyclohexylamine / 1-methyl-pyrrolidin-2-one / 1.5 h / 110 °C / Inert atmosphere

With hydrogenchloride; dmap; N-Methyldicyclohexylamine; dihydrogen peroxide; triethylamine; sodium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; 5: |Heck Reaction;

DOI:10.1021/acs.jmedchem.8b00182

upstream raw materials:

2-cyclohexyl-8-(vinylsulfonyl)-1,3,8-triazaspiro[4.5]dec-1-en-4-one

N-(4-bromo-3,5-dimethylphenyl)acetamide

4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 2-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate

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